


Jail House Romance

by CS_impala67



Category: Supernatural
Genre: Anal Fingering, Canon Divergence, Dubious Consent, M/M
Language: English
Status: In-Progress
Published: 2019-08-31
Updated: 2019-09-04
Packaged: 2020-10-04 07:24:53
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 1,875
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20467250
Author URL: https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67
Summary: Dean and Sam are captured after trying to expell Lucifer from the President's body. Unfortunately, no one believes they are the good guys





	1. Booking

**Author's Note:**

> Ok so i will be adding to this in the future but not sure how often. Eventually Destiel will happen.
> 
> In this story, it happens around the time that the boys got captured after dealing with Lucifer in the President's body. However it's not exactly canon because Castiel will be a new character that the boys haven't come across yet.

The guards lead them into the high security detention center. Of course when you are suspected to have killed the president, they would want you heavily secured. They were basically dragged, in their handcuffs and dirty clothes, into a complex that looked like it was pretty secure. Which would suck for them. Dean knew that his mom would look for them but the more security a place has, the harder it would be for them to find him and Sam. 

Dean, absorbed in his own thoughts, was abruptly shoved into a room with his brother. They were both made to sit in chairs on the right side of the room. There was a hard metal table on the other side that looked like it was for interrogation, especially because you could see the place on the table where they could attach their handcuffs.the guards left them alone in the room.

"What do you think they are planning on doing to us?" Sam asked.

"What do you think Sammy? They are gonna question us and obviously we can't tell the truth because then they will just label us freaking crazy. I mean, who in their right mind will believe we were trying to help, and that Lucifer was possessing the president? No one, obviously. So right now, we are stuck here till Mom figures out how to get us out of here." Dean replied, resigned to the fact that they were pretty helpless right now.

It was about a half hour later that a man walked into the room to address the Winchester brothers. " So it seems you boys refuse to talk?" He asked.  
Neither brother responded.  
"Ok. So I see talking will not solve this. Well let me introduce myself. My name is James and I will be in charge of you two while we get information and book you into our high security facility. Does anyone want to guess what the first step is?" He asked. 

Neither brother answered. " no one? Ok, i'll tell you. Strip and cavity searches!" James exclaimed. He sounded far more excited than he should. And his statement filled the Winchester brothers with dread. Both for different reasons though.

"Ok Sam, you are first." James stated. He walked over to Sam and pulled him up by the cuffs holding his arms behind his back. He dragged Sam over to the table to the other side of the room. He then pushed Sam's upper half over the table.  
" What the fuck are you doing?!" Sam yelled.

"I told you we were gonna strip and cavity search you. If you don't comply right now we will be forced to restrain you. Either way the search will happen. It's up to you how it's done."

Sam seemed to realise it would be easier to just do what they said without fighting."Alright fine, whatever just do it." He said. So after a thorough cavity search, he was allowed to re-dress and sat back in his chair. 

Unfortunately for Dean, that meant it was his turn now. The guard grabbed Dean's arm and brought him over to the table. He told him to bend over it.  
"Fuck you. I ain't bending over for anybody" Dean yelled at the guard.  
"If you don't comply, we can make his time here hell for Sam" James stated.  
That stopped Dean. He didn't want Sam to have to deal with any of this. And it probably wouldn't be that bad. He wasn't worried about a cavity search hurting or anything like that. He had a private reason why he didn't want it done. And he hoped no one ever learned his secret.

So to protect Sam, Dean bent over the table. He let the guard handcuff him to the table. The guard James came up behind him and reached around him to undo his pants. He then pulled Dean's pants and underwear down to his ankles.  
Dean felt so exposed. He could feel his ass standing out in the cold air and it was making him very anxious. The next thing he knew, James was spreading his cheeks and exposing his hole. Dean felt the cool air hitting his hole and it was turning him on, despite the fact that he didn't want it to. Dean heard another person come into the room. They came over to the table. Dean felt James' fingers leave him and the other guys' hands spread his cheeks wide. He then heard James speaking to the other man.  
"Thanks Steve, hold him open while I search his ass for any illegal substance." James said

Dean could feel Steve pulling his cheeks apart. Then he felt lube being smeared across his hole. Once he was sufficiently wet, he felt James start to work a finger into him. It was such a foreign thing. James worked his finger in and out of Dean's hole. He added a second finger and hit Dean's prostate a few times. Dean was bent over a table with his dick hanging out and every time James hit his prostate, Dean's dick leaked. All too soon, Dean came on the floor of the examination room while his cavity search was happening. He felt humiliated. He shouldn't have gotten off on that and it made him feel dirty.  
James removed his fingers from Dean's ass. "I have found no illegal substances inside this prisoner. You can bring them both to their cells and we will talk again tomorrow." James said.

"Good" stated Steve. "I need to use the bathroom and then we can finish  
processing these prisoners." He said

Dean was lead over to the chair next to his brother. His dick was still half hard and there was no way Sam missed it. Dean prayed he wouldn't ask questions. Of course luck wasn't on his side.

"Dean are you ok?" Sam asked.  
"Of course I am Sammy. Why wouldn't I be." Dean deflected.

"Yeah but you seem pretty out of it and upset." 

"Yeah Sam i know. I'm fine dont worry."

"Ok then why were you hard when you were finished with your cavity search?" Dam asked.

Dean froze. He didn't know how to answer. He never expected to actually have to have this conversation with Sam. Dean wasn't out. And he knew Sam would probably be ok with it but he never wanted to chance it before. Now it seemed like he had no choice but to address it. 

"Ok Sam. Yes there is something ive wanted to tell you for awhile. But ive always been afraid to so it." Dean said, looking at the floor so he didn't have to look into Sam's eyes. 

"What is it Dean? You know you can tell me anything."

"Well, i mean it's probably not a huge surprise. But I'm gay." Dean whispered as he looked anywhere but Sam's eyes. He was too afraid to see the judgement there.

"You're gay?" Sam questioned, looking very confused.

"Yeah."

" Are you sure? You really think you are gay?" Sam sounded so confused.

"Ugh yes Sam im sure. Im 40 years old. I think I know what I am by now. You can't be too surprised. You Really never saw me checking out guys?" Dean asked

" Yeah i've seen you checking out guys but honestly? I thought you were Bisexual. You've been with countless women so I'd never think you were actually gay. Like I said, maybe bisexual." Sam said honestly.

They could both hear guards about to come in the room to take them to their cells and didn't have much time currently.

" Alright so we don't have much time and I'll explain it all soon. But yes I'm gay and i love you Sam.  
And once we get out of here i promise ill tell you everything. Chick flick moment to the max" 

...to be continued.


	2. Realizing

The guards came around to the Winchester boys' cell and decided that it would probably be best if they kept the boys together. This way they could both see what was going on with each other's interrogation. Maybe that would get either man to talk.  
Of Course that didn't happen as they planned. The brothers seemed way more close than any brothers should. But that wouldn't stop them. They needed to know what was going on in order to protect the Country and their President.  
James was the first guard to unlock the boy's cage and try to get any information after the first search.  
"Sam. Come here right now." he ordered. Of course Sam did not want to comply. But honestly? What else was he supposed to do right now? Sam was locked in a high security prison. With not much hope to escape. So he did the only thing that seemed logical in this case. He complied. And James took him out of the cell. Away from anywhere Dean could see. And that didn't sit well with Dean. He needed to see where his brother went. And he was about to flip out and start banging on his cell door if it wasn't for Steve. Steve walked into Dean's cell after Sam was taken away. Dean was pissed and wanted nothing to do with one of the guards that violated him and made him essentially come out to his brother. But apparently, Steve wanted something else. 

"I am very sorry that you have had to deal with being in prison. And I am sorry that I played any part in it. And I know you don't belong here and you are telling the truth about the President and Lucifer, and i know no-one else will ever believe you. I do. And I am working on a way to get you out of here. You and your brother. Here they know me as Steve. But that is not my real name. And I am not a human guard. I promise I will get you both out of here. And you will continue protecting humanity as you always have." Steve continued. And then Steve disappeared. The Winchesters did not know what to think now. Who the hell was protecting them and what was Steve's real name?  
...to be continued


	3. What the Hell did we get ourselves into?

Dean didn't know what to do about 'Steve's' declaration. On one hand, he helped the other guard essentially violate him. But maybe he has at least someone in his corner here. Someone who knew about the supernatural and that the Winchesters were a huge part of eradicating those threats. Everyone else they tried to explain to had pretty much wrote them off as crazy. But not Steve. He seemed to fully believe them. That could be a huge advantage to them getting out of this hell hole.  
As Dean was thinking, the cell door opened up and Sam was thrown on the floor at his feet and then the cell door closed again. He looked terrible. Dean picked him up off the floor and got him into bed. He looked like he was put through the ringer. The only thing he said before succumbing to sleep left Dean's senses on full alert.

"Man, I Thought the cavity search was bad but you have no idea Dean..." and Sammy was out cold.

Fuck. What had they gotten themselves into?


End file.
